N-Phenyl-2-p-tolylthiazole-4-carboxamide derivatives: Syn-thesis and cytotoxicity evaluation as anticancer agents | ||
| Iranian Journal of Basic Medical Sciences | ||
| مقاله 6، دوره 17، شماره 7، مهر 2014، صفحه 502-508 اصل مقاله (1.53 M) | ||
| نوع مقاله: Original Article | ||
| شناسه دیجیتال (DOI): 10.22038/ijbms.2014.3029 | ||
| نویسندگان | ||
| Ahmad Mohammadi-Farani1؛ Alireza Foroumadi2؛ Monireh Rezvani Kashani3؛ Alireza Aliabadi* 4 | ||
| 1Novel Drug Delivery Research Center, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran 2 Department of Pharmacology, Toxicology and Medical Services, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran | ||
| 2Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran | ||
| 3Students Research Committee, Kermanshah University of Medical Sciences, Kermanshah, Iran 5 Department of Medicinal Chemistry, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran | ||
| 4Novel Drug Delivery Research Center, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran Department of Medicinal Chemistry, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran | ||
| چکیده | ||
| Objective(s):According to the prevalence of neoplastic diseases, there is a deep necessity for discovery of novel anticancer drugs in the field of medicinal chemistry. In the current study, a new series ofphenylthiazole derivatives(compounds 4a-4f) was synthesizedand theiranticancer activity was assessed in vitro. Materials and Methods:All synthesized derivatives were evaluated towards three human cancerous cell lines of SKNMC (Neuroblastoma), Hep-G2 (Human hepatocarcinoma) and MCF-7 cell (Breast cancer) using MTT assay and obtained values (IC50 ± SD) were compared with doxorubicin. Results:Unfortunately, none of the synthesized compounds showed superior activity than doxorubicin against cancerous cell lines. MCF-7 cell line was the most resistant cell line against tested compounds. Compounds 4c with para nitro (IC50 = 10.8 ± 0.08 µM) and 4d with meta chlorine (IC50 = 11.6 ± 0.12 µM) moieties exerted thehighest cytotoxic effects towardsSKNMC and Hep-G2 cell lines respectively. Conclusion: A new series of phenylthiazole derivatives were synthesized and their anticancer activity was assessed against cancerous cell lines. More structural modifications and derivatization is necessary to achieve to the more potent compounds. | ||
| کلیدواژهها | ||
| Anticancer؛ Cytotoxicity؛ Synthesis؛ Thiazole | ||
| مراجع | ||
|
1.Harford JB. Breast-cancer early detection in low-income and middle-income countries: do what you can versus one size fits all. Lancet Oncol 2011; 12:306-312.
2.Nussbaumer S, Bonnabry P, Veuthey J, Fleury-Souverain S. Analysis of anticancer drugs: A review. Talanta 2011; 85:2265-2289.
3.Porter AC, Vaillancourt RR. Tyrosine kinase receptor-activated signal transduction pathways which lead to oncogenesis. Oncogene 1998; 16:1343-1352.
4.Mousavi SH, Tayarani-Najaran Z, Hersey P. Apoptosis: from signalling pathways to therapeutic tools. Iran J Basic Med Sci 2008; 11:121-142.
5.Aliabadi A, Eghbalian E, Kiani A. Synthesis and cytotoxicity evaluation of a series of 1,3,4-thiadiazole based compounds as anticancer agents. Iran J Basic Med Sci 2013; 16:1133-1138.
6.Madhusudan S, Ganesan TS. Tyrosine kinase inhibitors in cancer therapy. Clin Biochem 2004; 37:618-635.
7.Kemnitzer W, Kuemmerle J, Jiang S, Zhang H-Z, Sirisoma N, Kasibhatla S, et al. Discovery of 1-benzoyl-3-cyanopyrrolo[1,2-a]quinolines as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. Part 1: Structure-activity relationships of the 1- and 3-positions. Bioorg Med Chem Lett 2008; 18:6259-6264.
8.Albreht T, Mckee M, Alexe DM, Coleman MP, Martin-Moreno JM. Making progress against cancer in Europe in 2008. Eur J cancer 2008; 44:1451-1456.
9.Ferlay J, Autier P, Boniol M, Heanue M, Colombet M, Boyle P. Estimates of the cancer incidence and mortality in Europe in 2006. Ann Oncol 2007; 18:581-592.
10.Jemal A, Siegel R, Ward E, Murray T, Xu J, Smigal C, et al. Cancer Statistics, 2006. Cancer J Clin 2006; 56:106-130.
11.Bhuran HA, Kini SJ. Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors. J Mol Graph Model 2010; 29:32-37.
12.Siddiqui N, Faiz Arshad M, Ahsan W, Shamsher Alam M. Thiazoles: a valuable insight into the recent advances and biological activities. Int J Pharm Sci Drug Res 2009; 1:136-143.
13.De S, Adhikari S, Tilak-Jain J, Menon VP, Devasagayam TPA. Antioxidant activity of an aminothiazole compound: possible mechanism. Chem-Biol Interact 2008; 173:215-223.
14.Zaharia V, Ignat A, Palibroda N, Ngameni B, Kuete V, Fokunang CN, et al. Synthesis of some p-toluenesulfonyl-hydrazinothiazoles and their anticancer activity. Eur J Med Chem 2010; 45:5080-5085.
15.Aliabadi A, Shamsa F, Ostad SN, Emami S, Shafiee A, Davoodi J, et al. Synthesis and biological evaluation of 2-Phenylthiazole-4-carboxamide derivatives as anticancer agents. Eur J Med Chem 2010; 11:5384-5389.
16.Nazari Tarhan H, Hosseinzadeh L, Aliabadi A, Babak Gholamine, Foroumadi A. Cytotoxic and apoptogenic properties of 2-phenylthiazole-4-carboxamide derivatives in human carcinoma cell lines. J Rep Pharm Sci 2012; 1:1-7.
17.Aliabadi A, Foroumadi A, Safavi M, Kaboudian Ardestani S. Synthesis, molecular docking and cytotoxicity evaluation of 2-(4-substituted-benzyl)isoindoline-1,3-dione derivatives as anticancer agents. J Rep Pharm Sci 2012; 1:19-22.
18.Aliabadi A, Foroumadi A, Safavi M, Ardestani S. Synthesis, cytotoxicity assessment, and molecular docking of 4-Substituted-2-p-thiazole derivatives as probable c-Src and erb tyrosine kinase inhibitors. Croat Chem Acta 2013; 86: in press.
19.Mahmoodi M, Aliabadi A, Emami S, Safavi M, Rjabalian S, Mohagheghi MA, et al. Synthesis and in-vitro cytotoxicity of poly-functionalized 4-(2-arylthiazole-4-yl)-4H-chromenes. Arch Pharm Chem Life Sci 2010; 343:411-416.
20.Stankova IG, Videnov GI, Golovinsky EV, Jung G. Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification. J Peptide Sci 1999; 5:392-398.
21.Aliabadi A, Andisheh S, Tayarani-Najaran, Z, Tayarani-Najaran M. 2-(4-Fluorophenyl)-N-phenylacetamide derivatives as anticancer agents: synthesis and in vitro cytotoxicity evaluation. Iran J Pharm Res 2013; 3:267-271.
22.Aliabadi A, Hasanvand Z, Kiani A, Mirabdali SS. Syn-thesis and in vitro cytotoxicity assessment of N-(5-(Benzylthio)-1,3,4-thiadiazol-2-yl)-2-(4-(trifluoro- methyl)phenyl) aceta-mide with potential anticancer activity. Iran J Pharm Res, 2013; 4:687-693. | ||
|
آمار تعداد مشاهده مقاله: 2,995 تعداد دریافت فایل اصل مقاله: 1,626 |
||